Enhanced water-solubility, antibacterial activity and biocompatibility upon introducing sulfobetaine and quaternary ammonium to chitosan

被引:137
作者
Chen, Yuxiang [1 ]
Li, Jianna [2 ]
Li, Qingqing [1 ]
Shen, Yuanyuan [2 ]
Ge, Zaochuan [1 ]
Zhang, Wenwen [3 ]
Chen, Shiguo [1 ]
机构
[1] Shenzhen Univ, Guangdong Res Ctr Interfacial Engn Funct Mat, Nanshan Dist Key Lab Biopolymers & Safety Evaluat, Shenzhen Key Lab Polymer Sci & Technol,Coll Mat S, Shenzhen 518060, Peoples R China
[2] Shenzhen Univ, Hlth Sci Ctr, Shenzhen 518060, Peoples R China
[3] N Carolina State Univ, Raleigh, NC 27695 USA
基金
中国国家自然科学基金;
关键词
Chitosan; Biomaterials; Biocompatibility; Antibacterial; Zwitterion; GENE DELIVERY; POLYURETHANE COMPOSITES; GAS SENSITIVITY; HYDROGELS; NANOPARTICLES; DERIVATIVES; POLYMERS; CHLORIDE;
D O I
10.1016/j.carbpol.2016.01.073
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Chitosan (CS) has attracted much attention due to its good antibacterial activity and biocompatibility. However, CS is insoluble in neutral and alkaline aqueous solution, limiting its biomedical application to some extent. To circumvent this drawback, we have synthesized a novel N-quaternary ammonium-O-sulfobetaine-chitosan (Q(3)BCS) by introducing quaternary ammonium compound (QAC) and sulfobetaine, and its water-solubility, antibacterial activity and biocompatibility were evaluated compare to N-quaternary ammonium chitosan and native CS. The results showed that by introducing QAC, antibacterial activities and water-solubilities increase with degrees of substitution. The largest diameter zone of inhibition (DIZ) was improved from 0 (CS) to 15 mm (N-Q(3)CS). And the water solution became completely transparent from pH 6.5 to pH 11; the maximal waters-solubility was improved from almost 0% (CS) to 113% at pH 7 (N-Q(3)CS). More importantly, by further introducing sulfobetaine, cell survival rate of Q(3)BCS increased from 30% (N-Q(3)CS) to 85% at 2000 mu g/ml, which is even greater than that of native CS. Furthermore, hemolysis of Q(3)BCS was dropped sharply from 4.07% (N-Q3CS) to 0.06%, while the water solution and antibacterial activity were further improved significantly. This work proposes an efficient strategy to prepare CS derivatives with enhanced antibacterial activity, biocompatibility and water solubility. Additionally, these properties can be finely tailored by changing the feed ratio of CS, glycidyl trimethylammonium chloride and NCO-sulfobetaine. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:246 / 253
页数:8
相关论文
共 36 条
[1]   Chitin and chitosan in selected biomedical applications [J].
Anitha, A. ;
Sowmya, S. ;
Kumar, P. T. Sudheesh ;
Deepthi, S. ;
Chennazhi, K. P. ;
Ehrlich, H. ;
Tsurkan, M. ;
Jayakumar, R. .
PROGRESS IN POLYMER SCIENCE, 2014, 39 (09) :1644-1667
[2]   Restraint of the Differentiation of Mesenchymal Stem Cells by a Nonfouling Zwitterionic Hydrogel [J].
Bai, Tao ;
Sun, Fang ;
Zhang, Lei ;
Sinclair, Andrew ;
Liu, Sijun ;
Ella-Menye, Jean-Rene ;
Zheng, Ying ;
Jiang, Shaoyi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (47) :12729-12734
[3]   Rapid End-Group Modification of Polysaccharides for Biomaterial Applications in Regenerative Medicine [J].
Bondalapati, Somasekhar ;
Ruvinov, Emil ;
Kryukov, Olga ;
Cohen, Smadar ;
Brik, Ashraf .
MACROMOLECULAR RAPID COMMUNICATIONS, 2014, 35 (20) :1754-1762
[4]   Chitosan in nasal delivery systems for therapeutic drugs [J].
Casettari, Luca ;
Illum, Lisbeth .
JOURNAL OF CONTROLLED RELEASE, 2014, 190 :189-200
[5]   Gas sensitivity of carbon black/waterborne polyurethane composites [J].
Chen, SG ;
Hu, JW ;
Zhang, MQ ;
Li, MW ;
Rong, MZ .
CARBON, 2004, 42 (03) :645-651
[6]   Relationships between organic vapor adsorption behaviors and gas sensitivity of carbon black filled waterborne polyurethane composites [J].
Chen, Shi Guo ;
Hu, Xian Lei ;
Hu, Jing ;
Zhang, Ming Qiu ;
Rong, Min Zhi ;
Zheng, Qiang .
SENSORS AND ACTUATORS B-CHEMICAL, 2006, 119 (01) :110-117
[7]   Synergistic antibacterial mechanism and coating application of copper/titanium dioxide nanoparticles [J].
Chen, Shiguo ;
Guo, Yujuan ;
Zhong, Huanqiong ;
Chen, Shaojun ;
Li, Jianna ;
Ge, Zaochuan ;
Tang, Jiaoning .
CHEMICAL ENGINEERING JOURNAL, 2014, 256 :238-246
[8]   Environmentally Friendly Antibacterial Cotton Textiles Finished with Siloxane Sulfopropylbetaine [J].
Chen, Shiguo ;
Chen, Shaojun ;
Jiang, Song ;
Xiong, Meiling ;
Luo, Junxuan ;
Tang, Jiaoning ;
Ge, Zaochuan .
ACS APPLIED MATERIALS & INTERFACES, 2011, 3 (04) :1154-1162
[9]   Study of zwitterionic sulfopropylbetaine containing reactive siloxanes for application in antibacterial materials [J].
Chen, Shiguo ;
Chen, Shaojun ;
Jiang, Song ;
Mo, Yangmiao ;
Luo, Junxuan ;
Tang, Jiaoning ;
Ge, Zaochuan .
COLLOIDS AND SURFACES B-BIOINTERFACES, 2011, 85 (02) :323-329
[10]   Enhanced water-solubility and mucoadhesion of N,N,N-trimethyl-N-gluconate-N-homocysteine thiolactone chitosan [J].
Chivangkul, Tawroong ;
Pengprecha, Somchai ;
Padungros, Panuwat ;
Siraleartmukul, Krisana ;
Prasongsuk, Sehanat ;
Muangsin, Nongnuj .
CARBOHYDRATE POLYMERS, 2014, 108 :224-231